A Domino Epoxide Ring-Opening Xanthate Migration Reaction: An Alternative Entry to Thiosugars

MANGIONE, MARÍA I.; SPANEVELLO, ROLANDO A.; SUÁREZ, ALEJANDRA G.; COMBA, MARÍA B.; SAROTTI, ARIEL M.; MANGIONE, MARÍA I.; SPANEVELLO, ROLANDO A.; SUÁREZ, ALEJANDRA G.; COMBA, MARÍA B.; SAROTTI, ARIEL M.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

WILEY-V C H VERLAG GMBH

Año: 2018 vol. 2018 p. 6848 - 6856

1434-193X

A sterereospecific and efficient synthesis of thiosugars derived from levoglucosenone and methyl α-d-glucopyranoside was developed by a domino epoxide ring opening- xanthate migration to afford 1,3-oxathiolane-2-thiones in high yields. The stereochemical outcome of the new C?S bond was defined by the configuration of the starting materials. The 1,3-oxathiolane-2-thiones were subsequently submitted to a second tandem reaction affording the corresponding 2,3-episulfide alcohols. The thiosugars obtained are useful building blocks for the synthesis of thiooligosaccharides with potential biological properties.